Publikace UTB
Repozitář publikační činnosti UTB

Polyglobalide-based porous networks containing poly(ethylene glycol) structures prepared by photoinitiated thiol-ene coupling

Repozitář DSpace/Manakin

Zobrazit minimální záznam


dc.title Polyglobalide-based porous networks containing poly(ethylene glycol) structures prepared by photoinitiated thiol-ene coupling en
dc.contributor.author Savin, Corina L.
dc.contributor.author Peptu, Cristian
dc.contributor.author Kroneková, Zuzana
dc.contributor.author Sedlačík, Michal
dc.contributor.author Mrlík, Miroslav
dc.contributor.author Sasinková, Vlasta
dc.contributor.author Peptu, Catalina A.
dc.contributor.author Popa, Marcel
dc.contributor.author Mosnáček, Jaroslav
dc.relation.ispartof Biomacromolecules
dc.identifier.issn 1525-7797 Scopus Sources, Sherpa/RoMEO, JCR
dc.date.issued 2018
utb.relation.volume 19
utb.relation.issue 8
dc.citation.spage 3331
dc.citation.epage 3342
dc.type article
dc.language.iso en
dc.publisher American Chemical Society
dc.identifier.doi 10.1021/acs.biomac.8b00634
dc.relation.uri https://pubs.acs.org/doi/10.1021/acs.biomac.8b00634
dc.description.abstract The high interest in polymers from natural resources prompted us to investigate the use of enzymatically synthesized polyglobalide (PGL) in the preparation of polymer networks with potential applications as biomaterials for drug delivery devices. Polymer networks were obtained under mild conditions by photoinitiated thiol-ene coupling between PGL and a poly(ethylene glycol-co-thiomalate) (PEG-SH) copolymer obtained by polycondensation. The obtained polymer networks were thoroughly characterized by Raman spectroscopy, scanning electron microscopy, titration of thiol groups and elemental analysis. Our study took into consideration the synthesis parameters for the polymer networks, such as the total polymer concentration and the SH/C=C functionality molar ratio. Swelling in both THF and water was assessed, and the potential of the materials for drug delivery was determined. The scanning electron microscopy images showed that the prepared polymer networks may have different morphologies ranging from homogeneous polymer materials to macroporous structures. Additionally, the prepared materials were found to be suitable from a cytotoxicity point of view, enabling their application as biomaterials for drug delivery devices. © 2018 American Chemical Society. en
utb.faculty University Institute
dc.identifier.uri http://hdl.handle.net/10563/1008162
utb.identifier.obdid 43879686
utb.identifier.scopus 2-s2.0-85048852858
utb.identifier.wok 000441852400016
utb.identifier.pubmed 29920197
utb.identifier.coden BOMAF
utb.source j-scopus
dc.date.accessioned 2018-08-30T13:31:23Z
dc.date.available 2018-08-30T13:31:23Z
dc.description.sponsorship SASPRO Programme of the Slovak Academy of Sciences [1628/03/02]; People Programme (Marie Curie Actions) European Union's Seventh Framework Programme under REA Grant [609427]; National Scholarship Programme of the Slovak Republic [18428]; Ministry of Education, Youth and Sports of the Czech Republic through program NPU I [LO1504]; [APVV-15-0545]; [VEGA 2/0158/17]; [VEGA 2/0124/18]
utb.ou Centre of Polymer Systems
utb.contributor.internalauthor Sedlačík, Michal
utb.contributor.internalauthor Mrlík, Miroslav
utb.fulltext.affiliation Corina L. Savin,†,‡ Cristian Peptu,*,†,§ Zuzana Kroneková,† Michal Sedlačík,∥ Miroslav Mrlik,∥ Vlasta Sasinková,⊥ Catalina A. Peptu,‡ Marcel Popa,‡,# and Jaroslav Mosnáček*,† † Polymer Institute of the Slovak Academy of Sciences, Dubravska cesta 9, 84541 Bratislava, Slovakia ‡ Department of Natural and Synthetic Polymers, Faculty of Chemical Engineering and Environmental Protection, “Gheorghe Asachi” Technical University of Iaşi, 700050 Iaşi, Romania § “Petru Poni” Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41A, 700487 Iaşi, Romania ∥ Centre of Polymer Systems, University Institute, Tomas Bata University in Zlin, Trida T. Bati 5678, 760 01 Zlin, Czech Republic ⊥ Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, 845 38 Bratislava, Slovakia # Academy of Romanian Scientists, 010071 Bucuresti, Romania
utb.fulltext.dates Received: April 16, 2018 Revised: June 7, 2018 Published: June 19, 2018
utb.fulltext.references (1) Morgan, C. R.; Magnotta, F.; Ketley, A. D. Thiol/ene photocurable polymers. J. Polym. Sci., Polym. Chem. Ed. 1977, 15, 627−645. (2) Morgan, C. R.; Ketley, A. D. (1978) The effect of phosphines on thiol/ene curing systems. J. Polym. Sci., Polym. Lett. Ed. 1978, 16, 75−79. (3) Koo, S. P. S.; Stamenović, M. M.; Prasath, R. A.; Inglis, A. J.; Du Prez, F. E.; Barner-Kowollik, C.; Van Camp, W.; Junkers, T. Limitations of radical thiol-ene reactions for polymer-polymer conjugation. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 1699−1713. (4) Hoyle, C. E.; Bowman, C. N. Thiol- Ene Click Chemistry. Angew. Chem., Int. Ed. 2010, 49, 1540−1573. (5) Lowe, A. B. Thiol-ene “click” reactions and recent applications in polymer and materials synthesis. Polym. Chem. 2010, 1, 17−36. (6) Jaffry, U.; Muñoz-Bonilla, A.; Herrasti, P. Click chemistry reactions in polymer synthesis and modification. In Polymer Science: Research Advances, Practical Applications and Educational Aspects; Méndez-Vilas, A., Solano, A., Eds.; Formatex Reasearch Center: Badajoz, Spain, 2016; pp 139−149. (7) Lowe, A. B. Thiol−ene “click” reactions and recent applications in polymer and materials synthesis: a first update. Polym. Chem. 2014, 5, 4820−4870. (8) Derboven, P.; D’hooge, D. R.; Stamenovic, M. M.; Espeel, P.; Marin, G. B.; Du Prez, F. E.; Reyniers, M.-F. Kinetic modeling of radical thiol-ene chemistry for macromolecular design: importance of side reactions and diffusional limitations. Macromolecules 2013, 46 (5), 1732−1742. (9) Fairbanks, B. D.; Love, D. M.; Bowman, C. N. Efficient Polymer-Polymer Conjugation via Thiol-ene Click Reaction. Macromol. Chem. Phys. 2017, 218, 1700073. (10) van der Meulen, I.; de Geus, M.; Antheunis, H.; Deumens, R.; Joosten, E. A. J.; Koning, C. E.; Heise, A. Polymers from functional macrolactones as potential biomaterials: Enzymatic ring opening polymerization, biodegradation, and biocompatibility. Biomacromolecules 2008, 9, 3404−3410. (11) Kraft, P.; Bajgrowicz, J. A.; Denis, C.; Frater, G. Odds and Trends: Recent Developments in the Chemistry of Odorants Note on trademarks: Words which we know or have reason to believe constitute registered trademarks (R) are designated as such. However, neither the presence nor absence of such designation should be regarded as affecting the legal status of any trademark. Note on perfume analysis: The quoted percentages of perfume raw materials in market products are rounded figures. They are often derived from area percentages from the GC (FID) analysis and are thus subject to analytical error. Angew. Chem., Int. Ed. 2000, 39, 2980−3010. (12) Williams, A. S. The Synthesis of Macrocyclic Musks. Synthesis 1999, 1999 (10), 1707−1723. (13) Ates, Z.; Thornton, P. D.; Heise, A. Side-chain functionalisation of unsaturated polyesters from ring-opening polymerisation of macrolactones by thiol−ene click chemistry. Polym. Chem. 2011, 2, 309−312. (14) Ates, Z.; Heise, A.; et al. Functional Brush Decorated Poly(globalide) Films by ARGET-ATRP for Bioconjugation. Macromol. Biosci. 2014, 14, 1600−1608. (15) Ates, Z.; Heise, A. Functional films from unsaturated poly(macrolactones) by thiol−ene cross-linking and functionalization. Polym. Chem. 2014, 5, 2936−2941. (16) Claudino, M.; van der Meulen, I.; Trey, S.; Jonsson, M.; Heise, A.; Johansson, M. Photoinduced Thiol-Ene Crosslinking of Globalide/-Caprolactone Copolymers: curing performance and resulting thermoset properties. J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 16−24. (17) de Oliveira, F. C. S.; Olvera, D.; Sawkins, M. J.; Cryan, S.-A.; Kimmins, S. D.; da Silva, T. E.; Kelly, D. J.; Duffy, G. P.; Kearney, C.; Heise, A. Direct UV-Triggered Thiol-ene Cross-Linking of Electrospun Polyester Fibers from Unsaturated Poly(macrolactone)s and Their Drug Loading by Solvent Swelling. Biomacromolecules 2017, 18 (12), 4292−4298. (18) Zhu, W.; Gao, L.; Luo, Q.; Gao, C.; Zha, G.; Shen, Z.; Li, X. Metal and light free, click” hydrogels for prevention of post - operative peritoneal adhesion. Polym. Chem. 2014, 5, 2018−2026. (19) Du, H.; Zha, G.; Gao, L.; Wang, H.; Li, X.; Shen, Z.; Zhu, W. Fully biodegradable antibacterial hydrogels via thiol−ene “click” chemistry. Polym. Chem. 2014, 5, 4002−4008. (20) Huang, Y.; Sun, R.; Luo, Q.; Wang, Y.; Zhang, K.; Deng, X.; Zhu, W.; Li, X.; Shen, Z. In situ fabrication of paclitaxel-loaded corecrosslinked micelles via thiol-ene “click” chemistry for reductionresponsive drug release. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 99−107. (21) Erdodi, G.; Kennedy, J. P. Third-generation amphiphilic conetworks. I. Synthesis and swelling behavior of poly(N,N-dimethyl acrylamide)/polydimethylsiloxane conetworks. Prog. Polym. Sci. 2006, 31, 1−18. (22) Raghavan, S. R.; Cipriano, B. H. Gel Formation: Phase Diagrams Using Tabletop Rheology and Calorimetry, Molecular Gels, Materials with Self-Assembled Fibrilar Networks; Weiss, R. G., Terech, P., Eds.; Springer: Dordrecht, The Netherlands, 2006; Chapter 8. (23) Rohrer, J.; Partenhauser, A.; Zupančič, O.; Leonavičiu̅tė, G.; Podričnik, S.; Bernkop-Schnürch, A. Thiolated gelatin films: Renaissance of gelatin as sustained intraoral dosage form. Eur. Polym. J. 2017, 87, 48−59. (24) Mongkhontreerat, S.; Öberg, K.; Erixon, L.; Löwenhielm, P.; Hult, A.; Malkoch, M. UV initiated thiol−ene chemistry: a facile and modular synthetic methodology for the construction of functional 3D networks with tunable properties. J. Mater. Chem. A 2013, 1, 13732−13737. (25) Nguyen, K. D. Q.; Megone, W. V.; Kong, D.; Gautrot, J. Thiolene cross-linking and functionalisation of Polydimethylsiloxane for biomedical applications. Polym. Chem. 2016, 7, 5281−5293. (26) Wu, D.; Xu, F.; Sun, B.; Fu, R.; He, H.; Matyjaszewski, K. Design and preparation of porous polymers. Chem. Rev. 2012, 112 (7), 3959−4015. (27) Li, Q.; Zhou, H.; Hoyle, C. E. The effect of thiol and ene structures on thiol−ene networks: Photopolymerization, physical, mechanical and optical properties,. Polymer 2009, 50, 2237−2245. (28) Munday, R. Toxicity of thiols and disulphides: Involvement of free-radical species. Free Radical Biol. Med. 1989, 7, 659−673. (29) Ritger, P. L.; Peppas, N. A. A simple equation for description of solute release I. Fickian and non-Fickian release from non-swellable devices in the form of slabs, spheres, cylinders or discs,. J. Controlled Release 1987, 5 (1), 23−36.
utb.fulltext.sponsorship C.P. acknowledges that this work is financed by the SASPRO Programme of the Slovak Academy of Sciences (Grant Agreement No.: 1628/03/02). Part of the research leading to these results received funding from the People Programme (Marie Curie Actions) European Union’s Seventh Framework Programme under REA Grant Agreement No. 609427. J.M. thanks projects APVV-15-0545 and VEGA 2/0158/17, and the work of Z.K. was also supported by VEGA 2/0124/18. C.S. acknowledges the support of the National Scholarship Programme of the Slovak Republic for the Support of Mobility of Students, Ph.D. Students, University Teachers, Researchers and Artists (Grant Agreement No.: 18428). M.S. and M.M. are thankful for the support of the Ministry of Education, Youth and Sports of the Czech Republic through program NPU I (LO1504).
utb.wos.affiliation [Savin, Corina L.; Peptu, Cristian; Kronekova, Zuzana; Mosnacek, Jaroslav] Slovak Acad Sci, Inst Polymer, Dubravska Cesta 9, Bratislava 84541, Slovakia; [Savin, Corina L.; Peptu, Catalina A.; Popa, Marcel] Gheorghe Asachi Tech Univ Iasi, Fac Chem Engn & Environm Protect, Dept Nat & Synthet Polymers, Iasi 700050, Romania; [Peptu, Cristian] Petru Poni Inst Macromol Chem, Aleea Grigore Ghica Voda 41A, Iasi 700487, Romania; [Sedlacik, Michal; Mrlik, Miroslav] Tomas Bata Univ Zlin, Univ Inst, Ctr Polymer Syst, Trida T Bati 5678, Zlin 76001, Czech Republic; [Sasinkova, Vlasta] Slovak Acad Sci, Inst Chem, Dubravska Cesta 9, Bratislava 84538, Slovakia; [Popa, Marcel] Acad Romanian Scientists, Bucharest 010071, Romania
utb.scopus.affiliation Polymer Institute, Slovak Academy of Sciences, Dubravska cesta 9, Bratislava, Slovakia; Department of Natural and Synthetic Polymers, Faculty of Chemical Engineering and Environmental Protection, Gheorghe Asachi Technical University of Iaşi, Iaşi, Romania; Petru Poni Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41A, Iaşi, Romania; Centre of Polymer Systems, University Institute, Tomas Bata University in Zlin, Trida T. Bati 5678, Zlin, Czech Republic; Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, Bratislava, Slovakia; Academy of Romanian Scientists, Bucuresti, Romania
utb.fulltext.projects SASPRO 1628/03/02
utb.fulltext.projects REA 609427
utb.fulltext.projects APVV-15-0545
utb.fulltext.projects VEGA 2/0158/17
utb.fulltext.projects VEGA 2/0124/18
utb.fulltext.projects 18428
utb.fulltext.projects LO1504
Find Full text

Soubory tohoto záznamu

Zobrazit minimální záznam